5 Things I’m Glad I Experienced Before I Started My App: With Greg Woock, CEO Of Sideline

I had the pleasure of interviewing Greg Woock, CEO and founder of Pinger, developers of iTunes top grossing business app, Sideline. He began his career bringing sound to computers with the SoundBlaster at Creative Labs, took the lead in developing and establishing the modern smartphone business model at Handspring with the Treo, was a CEO for Richard Branson at Virgin Electronics and now he is helping small businesses communicate better and grow faster with Sideline.

Thank you so much for doing this with us! What is your “backstory”?

I grew up playing guitar in bands and wasn’t interested in school. School was boring and I thought I knew everything anyway so I didn’t attend much. There were classes where I showed up only once or twice. But for a few heroic teachers and a great dean, I would have been expelled. They gave me a million second chances. When it came time to graduate, I had roughly 11 of the 100 plus credits necessary, so I sat home on graduation day while everyone I thought I was so much smarter than graduated. That was a pretty dark day. I drifted for a few years and then my high school sweetheart told me we were having a child. That changed things. I realized life had started a long time ago — I just hadn’t been participating. I got my high school diploma, got into a liberal arts college and studied film to make television commercials. When I was in film school, I saw how computers were influencing film production and became increasingly interested in technology. It was obvious that personal computing would have a huge impact on the world. I wanted to be a part of it, so I made the jump to work in technology. I graduated in 3 years with honors. My then girlfriend is now my wife and that child runs sales and marketing at my company. He has two other siblings that work at the company as well, part time…while GOING TO SCHOOL.

Can you share the funniest or most interesting story that happened to you since you started your company?

One of my investors is Kleiner Perkins, Caufield, Byers — a legendary venture capital firm in Silicon Valley. They’re great at getting get their CEOs together annually to meet and discuss important ideas and topics. Years ago, former Vice President Al Gore premiered “An Inconvenient Truth” at one of their CEO events. The film was obviously very powerful and affected everyone in the room. Adding to that impact, the assembled group was called upon by KPCB’s de facto leader, John Doerr, to help solve the problem of global warming. Everyone left the event seriously pondering the future of our planet and our individual obligations to help.

When the event was over, a group of us waited in the valet line for our cars to be brought around.

Former Vice President Gore was standing off to the side in conversation, but facing us. This was pre-Tesla and as the cars starting showing up, it became apparent that the groups personal vehicle choices were not environmentally friendly. As the names of the vehicles were called out, the embarrassed owners of the vehicles came forward and reconciled their personal choices in front of the group. Unfortunately for me, I had arrived in the least environmentally friendly vehicle, an old Land Rover Defender which is one of those the Jeep-like trucks you see in Africa. There was an eruption of laughs and groans when it pulled up. Like everyone else in line that day, my personal choices were brought into crisp focus. The idea of personal environmental responsibility was no longer abstract. Shortly thereafter, I got a Prius, went solar and started asking myself what I can do to help reduce my impact on the environment on a regular basis.

So how does your company help people?

We make Sideline, a mobile application that provides a second number for your smartphone that works just like your first number. It is especially popular with small businesses who run entirely on mobile phones. Sideline does things like automatically reply to missed calls with the business’s logo and a text message so the business can engage customers better and faster. Sideline can also let that business number ring or receive texts on multiple employee devices. We have more features coming soon that further allow businesses to work smarter and grow faster.

What makes your business stand out? Can you share a story?

We empower small businesses by letting them communicate in new and unconventional ways. One of Sideline’s customers is a musician named Mikey Mike. Mikey was launching a new (Rick Rubin produced) single for Warner Brothers Records. He knew this was a big shot at success and wanted to do something really unique. He passed on social media in favor of a more disruptive way to reach people. He put up billboards all around Hollywood with a crazy wanted-poster-style picture of himself above a phone number. He got tens of thousands of people to call and text that number, which automatically triggered a picture message he set up with Sideline’s Smart Reply feature. That picture message was an invite to his birthday party, which launched the tour he’s on now. His marketing launch was crazy successful and really highlights how today’s entrepreneurs can embrace new technology to cut through the noise and connect with customers.

How have you used your success to bring goodness to the world?

First, we help small businesses run better and grow to their full potential by giving them a personalized set of business tools for their mobile phones. Having been a leader in many small businesses that were lucky enough to scale, I appreciate how transformative that growth is to customers, employees and investors.

What are your “5 things I wish someone told me before I Started my Business” and why?

Here is a combination of lessons I learned before I started my current business, and things I wish I knew before starting my current company.

Sweat the details once so that everyone else will sweat them forever- My first real job out of college was working for a large Japanese tech company. The head of my region was a serious, hard-working man who everyone was a bit scared of. One day he called me into his office. He was holding one of my expense reports and proceeded to tell me that he was rejecting it because a date on the receipt (for a $0.25 toll) didn’t match the date the expense was claimed.

After some back and forth, it was clear I had claimed the expense correctly, but he still rejected it on a technicality. I couldn’t believe he had nothing better to do than look at $0.25 toll receipts and check dates. Still, as time went on, we developed a great working relationship. When I left that company for another opportunity, he took me to dinner and asked if I remembered the expense report incident. I said, “Oh yes, I never forgot it.” That’s when he told me he never looked at my expense reports closely again, because he knew that from then on, I was the one looking at every detail in anything I handed him.

Take care of your people- My second job was working for a small, family-owned tech company called GB Marketing. One day, the owner, Tom was adversely affected by a lawsuit that froze his company’s assets. That day happened to be payday and instead of regular checks, he wrote us personal checks for payroll. The legal decision ended up being reversed and the company continued to be successful, but I never forgot that. On what must have been one of the scariest days of Tom’s life, he thought about his employees first, and without hesitation.

Cash is queen- I worked at smartphone pioneer Handspring where Donna Dubinsky was the CEO. Donna was one of the first female tech CEOs in Silicon Valley. She used to say, “Cash is queen,” all the time as a play on the commonly used, “cash is king” phrase. I always had two takeaways from her comment; 1) Money isn’t masculine or feminine. No cash = no business. 2) It was the only time I remember making the distinction that she was a female CEO. Leaders are leaders and gender doesn’t have anything to do with it.

Go where the customer is underserved- This is a Richard Branson line that always resonated with me because where the customer is underserved lies opportunity. You see the successful Virgin companies capitalize on this idea again and again.

Always look at the data… and look at it closely- Early in Pinger’s history, we had two messaging apps that we thought could change the game — the first required both sender and receiver to have the app. The second only needed a sender. The second app had way more users and was making more money so we dropped the first app. The app we dropped was almost exactly like one from a competitor that eventually exited the market at $19 billion. Had I peeled the data onion further, I would have seen that the absolute scale or users or revenue wasn’t the only valuable piece of data. The valuable piece of data I missed was the penetration rate in the market based on available users. That available market for the app we dropped eventually grew much larger than the market for the one we kept. Unless you look at the data closely, you may reach the wrong conclusions.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. :-)

I’d like to hang with Bill Murray. He’s is a Chicagoan and a Cub fan like me and I love his effortless, intelligent humor. He is great spontaneously (find his color commentary at Cub’s games on YouTube) and even better when he can prepare (his legendary appearances on David Letterman). Who wouldn’t want to hang out with Bill Murray?